US2880241A - Carbonylation synthesis reaction - Google Patents

Carbonylation synthesis reaction Download PDF

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Publication number
US2880241A
US2880241A US558409A US55840956A US2880241A US 2880241 A US2880241 A US 2880241A US 558409 A US558409 A US 558409A US 55840956 A US55840956 A US 55840956A US 2880241 A US2880241 A US 2880241A
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rhodium
catalyst
reaction
cobalt
hydrogen
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Vincent L Hughes
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Priority to NL98500D priority patent/NL98500C/xx
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions

Definitions

  • Cyclic olefins such as cyclohexene, styrene as well as olefin polymers such as diand tri-isobutylene and hexene are also useful in the present process.
  • monomeric olefins having 2 to carbon atoms in the molecule and polymers thereof may be used.
  • the synthesis gas mixture containing hydrogen and carbon monoxide may be obtained from any conventional source such as carbonaceous solids or gases in any manner known in the art and in any desired ratio of hydrogen to carbon monoxide.
  • the ratio of hydrogen to carbon monoxide which may be employed will generally range from about 0.5:1 to 10:1.
  • Generally low hydrogen to carbon monoxide ratios 0.5- 1.5 are preferred when aldehydes are the desired products; however, higher ratios (e.g. 2-4) are used when I high alcohol conversions are desired.
  • the reaction of present invention relates to the discovery of how to em:
  • rhodium and rhodium compounds as highly efiective carbonylation catalysts.
  • r r The present invention also relates 'to'the discovery of new compounds synthesized by the-instant process 'and which will be defined in greater detail hereinafter.
  • oxygenated organic compounds may be synthesized from olefins by areaction with carbon monoxide and hydrogen in the presence of catalysts containing cobalt under limited conditions known as oxo conditions.
  • the so-called oxo process employs.
  • the rhodium catalyst permits a more selective and a different kind of carbonylation.
  • dicyclopentadiene can be oxygenated at 100 C. using a rhodium-containing catalyst to form the unsaturated aldehyde whereas .said
  • Rhodium-containing catalysts are effective tools .for
  • the olefinic reactants which come within the scope of the present process may comprise pure olefin or hydrocarbon mixtures containing olefins. These olefins maybe broadly classified into two groups, diolefins and the mono-olefins.
  • the mono-olefins are represented by straight and branched chain compounds such as ethylene,
  • non-conjugated.v Representative of the non conjugated diolefins are dicyclopentadiene, the lower alkyl substituted dicylopentadienes, the terpenes and' vinylttively, it is essential that it be present in the form of a soluble product during the reaction. Elemental rhodium, inorganic or organic rhodium salts are examples of those substances which will form a soluble rhodium compound under the reaction conditions of the present process.
  • the rhodium may be in the form of a carbonyl which would include any rhodium carbonyl, hydrocarbonyl mixtures and complex compounds thereof. Accordingly the catalyst of this invention may be added as metallic rhodium, arhodium oxide, salt or any rhodium-containing composition of matter which can be maintained inthe form of a soluble rhodium compoun drunder said reaction conditions. More specifically rhodium dioxide, sesquioxide, halide, nitrate, sulfate, sulfite and salts of organic acids such as oleic, stearic, etc., may be employed.
  • the catalyst of this invention may be added as metallic rhodium, arhodium oxide, salt or any rhodium-containing composition of matter which can be maintained inthe form of a soluble rhodium compoun drunder said reaction conditions. More specifically rhodium dioxide, sesquioxide, halide, nitrate,
  • preferred rhodium compounds for this process are the above noted oxides and the chloride.
  • Rhodium oxides and chlorides are especially desirable since they are easily converted to the soluble forin and they represent the most effective form of rhodium from the standpoint of permitting fast reaction rates, good yields and low bottoms.
  • Rhodium carbonyls are usable and may be preformed in any known manner, to a form such as a solid crystalline material or in solution with an organic solvent, e.g., hexane, aldehyde, olefin, alcohol, etc., and either may be used in the reaction mixture as the catalyst.
  • Rhodium carbonyl may be made by any of the various methods known in the art among which, direct union ofcarbon monoxide with metallic rhodium or a rhodium salt at high pressures, is effective.
  • Rhodium carbonyl takes several forms. 2( )8 )3)w 4( )11)n and Rh(CO H.
  • the various forms of rhodium carbonyl as well as mixtures thereof are suitable catalytic materials for the present reaction. However, some are more desirable than others.
  • any of the above rhodium-containing catalysts may be supported on conventional carriers such 5 alumina, kieselguhr, silica, silica-alumina or any other carrier inert to the reaction.
  • the proportion of rhodium or rhodium compound to the carrier is not critical since the catalytic effect is due solely to the amount of rhodium per unit of olefin feed.
  • the rhodium compound when on a support should comprise from about 1% to 40% by weight based on rhodium to the carrier, with about 5% being preferred.
  • the catalyst concentration may vary over a range of from about 0.002 to 20.0 mole percent basedon the rhodium to the olefin, but the preferred range is 0.01-5
  • mole percent depend mainly on the temperature and the desired results. Generally, higher operating temperatures require less catalyst and result in the formation of more normal than branched isomer with increased bottoms yields. Conversely, lower temperatures require more catalyst which results in the production of branched chainisomer and low bottom yields.
  • the rhodium catalyzed process of the present invention affords improved yields of desirable products and at increased reaction rates as will appear more clearly from the following specific examples and data.
  • EXAMPLE 2 This example illustrates the preformation of soluble rhodium compounds in a hexane solution and use thereof in the present process..
  • rhodium may be recovered in a direct single step operation, as a catalytically active product.
  • the product recovered from the present process will contain dissolved rhodium therein.
  • the rhodium may be recovered from the product by treatment with water at elevated temperatures whereupon the rhodium components precipitate out in the aqueous phase generallyas amixture of metallic rhodium and oxides there- 'of.
  • Easy conversion of the precipitated rhodium to the active :oxide may be accomplished by any well-known oxidation technique such as treatment with air at elevated temperatures, e.g., 400 C.
  • Any rhodium remaining in the product in the form of a fine suspension after treatment with water may be recovered by flashing off the product.
  • it is generally preferred to add from about 5 to 40% by volume water at -200 C. Temperatures over about 200 C. are examples of water at -200 C.
  • Temperatures as low as 80 C. are also usable; however, to improve the rate of precipitation temperatures above 120 C. have been found to be advantageous.
  • the filtered material (rhodium) was dried and recycled to the reactor which was then charged with 500 ccs. of butene-1 and the above procedure repeated. At 150 C. the reaction proceeded smoothly and in the same manner as the first run.
  • EXAMPLE 4 550 ccs. of C olefin obtained by copolymerizing .butene-l, and propylene, and 0.31 gm. Rh O were added.
  • Butene-l was oxonated as above with 0.3 gm. rhodium 'oxide at 210 C. and H /CO (1:1) at 5200 p.s.i.g. The reaction was completed in one-half hour. After cooling :and venting the reactor, the material was hydrogenated over a nickel catalyst and the water white product was distilled. 65% of the product boiled in the range of the :amyl alcohols present.
  • EXAMPLE 6 This example further illustrates the eifect of rhodium on selective carbonylation.
  • the lower alkyl radicals may contain one, two or more carbon atoms and may be attached to any of the carbon atoms in the nucleus.
  • These aldehydes can be reacted with alcohol in the presence of an acid catalyst to form an acetal. This acetal can then be oxonated further to form the aldehyde derivative. This in turn can be hydrolyzed to give the dialdehyde and subsequently reduced to form a glycol.
  • the unsaturated mono-aldehyde of dicyclopentadiene may be reduced selectively to the unsaturated alcohol by the use of metal hydrides, which in turn may be oxonated further to form, after reduction, a glycol of dicyclopentadiene.
  • the volume of diluent employed may vary between l-6 volumes of diluent/volume of diolefin, preferably more than 2 volumes per volume of diolefin.
  • Percent Relative Temp., 0 Branched Reaction Rhodium Cobalt Isomer Rate may be used with about 0.0010.05% rhodium whereas at higher temperatures less cobalt and about 0.0005- 0.003% rhodium are satisfactory to give fast reactions.
  • Any of the aforementioned rhodium-containing catalysts may be used with any conventional cobalt-containing carbonylation catalyst.
  • a process'for producing oxygenated compounds by *the reaction of an olefinic hydrocarbon compound, carbon monoxide and hydrogen which comprises reacting said olefinic compound with carbon monoxide and hydrogen at temperatures between about 60-240 C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US558409A 1956-01-11 1956-01-11 Carbonylation synthesis reaction Expired - Lifetime US2880241A (en)

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US558409A US2880241A (en) 1956-01-11 1956-01-11 Carbonylation synthesis reaction

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Cited By (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3081357A (en) * 1960-05-24 1963-03-12 Du Pont Process for producing alkanediols
US3239566A (en) * 1960-07-22 1966-03-08 Shell Oil Co Hydroformylation of olefins
US3318913A (en) * 1965-09-22 1967-05-09 Shell Oil Co Process for producing alpha-methylgamma-butyrolactone
US3352924A (en) * 1963-01-23 1967-11-14 Exxon Research Engineering Co Carbonylation reactions
US3446839A (en) * 1965-09-20 1969-05-27 Shell Oil Co Production of alkyl hydroxy-pivalates
US3487112A (en) * 1967-04-27 1969-12-30 Monsanto Co Vapor phase hydroformylation process
US3501531A (en) * 1964-12-15 1970-03-17 Ethyl Corp Hydroformylation process
US3509221A (en) * 1965-07-09 1970-04-28 Shell Oil Co Production of cyclooctanemethanol
DE1793069A1 (de) * 1967-08-03 1972-02-03 Union Carbide Corp Verfahren zur Herstellung sauerstoffhaltiger Produkte
US3887489A (en) * 1972-11-24 1975-06-03 Monsanto Co Rhodium catalyst regeneration method
US4101450A (en) * 1977-05-09 1978-07-18 Celanese Corporation Catalyst for production of acetic acid
US4113781A (en) * 1973-08-11 1978-09-12 Basf Aktiengesellschaft Phenylpropanals
JPS5416418A (en) * 1977-06-21 1979-02-07 Johnson Matthey Co Ltd Process for preparing linear aldehyde
US4147725A (en) * 1978-03-22 1979-04-03 The Dow Chemical Company Process for preparing aniline compounds from amides with rhodium
US4229324A (en) * 1978-05-04 1980-10-21 Kao Soap Company, Limited Tricyclo-α,β-unsaturated aldehyde
US4262147A (en) * 1979-03-16 1981-04-14 The Dow Chemical Company Hydroformylation of dicyclopentadiene to its dimethanolic derivatives
US4270007A (en) * 1978-11-16 1981-05-26 Henkel Kommanditgesellschaft Auf Aktien Perfume aldehydes from hydroformylation of caryophyllene
US4283561A (en) * 1978-11-16 1981-08-11 Henkel Kommanditgesellschaft Auf Aktien Mixture of aldehydes resulting from hydroformylation of α-terpinene
US4298499A (en) * 1980-07-14 1981-11-03 Uop Inc. Recovery of catalysts
US4312779A (en) * 1980-09-25 1982-01-26 Uop Inc. Recovery of catalysts
US4320032A (en) * 1979-11-16 1982-03-16 Suntech, Inc. Catalyst for hydrogenation of aromatic dinitriles
US4334100A (en) * 1978-11-16 1982-06-08 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Production of aldehydes
US4340570A (en) * 1981-03-06 1982-07-20 The Halcon Sd Group, Inc. Recovery of rhodium from carbonylation residues
US4340569A (en) * 1981-03-06 1982-07-20 The Halcon Sd Group, Inc. Treatment of carbonylation residues
US4341741A (en) * 1981-03-06 1982-07-27 The Halcon Sd Group, Inc. Recovery of rhodium from carbonylation residues
WO1982003856A1 (en) * 1981-05-01 1982-11-11 Kodak Co Eastman Hydroformylation process
US4361711A (en) * 1981-12-18 1982-11-30 The Standard Oil Company Alcohols from olefins and synthesis gas
US4388477A (en) * 1981-06-02 1983-06-14 Eastman Kodak Company Hydroformylation process employing unmodified rhodium-cobalt catalyst
US4400547A (en) * 1981-04-10 1983-08-23 Eastman Kodak Company Hydroformylation process utilizing an unmodified rhodium catalyst and the stabilization and regeneration thereof
US4448984A (en) * 1982-03-02 1984-05-15 International Flavors & Fragrances Inc. Mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives
US4460795A (en) * 1982-03-02 1984-07-17 International Flavors & Fragrances Inc. Process for preparing mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives
US4476238A (en) * 1981-05-28 1984-10-09 The Halcon Sd Group, Inc. Separation of tars from carbonylation reaction mixtures
US4476237A (en) * 1981-05-28 1984-10-09 The Halcon Sd Group, Inc. Separation of tars from carbonylation reaction mixtures
US4587364A (en) * 1984-05-21 1986-05-06 Eastman Kodak Company Hydroformylation process employing unmodified osmium-cobalt catalyst
US4694109A (en) * 1986-06-13 1987-09-15 Eastman Kodak Company Chelate ligands for low pressure hydroformylation catalyst and process employing same
US4742178A (en) * 1986-11-10 1988-05-03 Eastman Kodak Company Low pressure hydroformylation of dienes
US5081313A (en) * 1989-06-22 1992-01-14 Basf Aktiengesellschaft Process for the preparation of 2,3-dialkoxypropanals
US5189105A (en) * 1987-02-09 1993-02-23 Mitsubishi Chemical Industries Limited Alcohol mixture for plasticizer
US5410091A (en) * 1994-06-02 1995-04-25 Quimica Oxal C.A. Rhodium catalyzed oxo process in tubular reactor
US5919987A (en) * 1994-03-16 1999-07-06 Basf Aktiengesellschaft Preparation of alcohols and/or aldehydes
US6365782B1 (en) 1999-07-02 2002-04-02 Mitsbushi Gas Chemical Company, Inc. Production of tricyclodecane dicarbaldehyde, pentacyclopentadecane dicarbaldehyde and corresponding dimethanols
EP1138751A3 (en) * 2000-03-27 2002-12-18 Toyota Jidosha Kabushiki Kaisha Method of manufacturing oxygenated fuel
WO2021021902A1 (en) 2019-07-29 2021-02-04 Eastman Chemical Company Process for the preparation of polyesters with recycled monomers from pyrolysis and methanolysis
WO2021021855A1 (en) 2019-07-29 2021-02-04 Eastman Chemical Company Recycle content cyclobutane diol polyester
US11319262B2 (en) 2019-10-31 2022-05-03 Eastman Chemical Company Processes and systems for making recycle content hydrocarbons
US11365357B2 (en) 2019-05-24 2022-06-21 Eastman Chemical Company Cracking C8+ fraction of pyoil
US11939534B2 (en) 2019-11-07 2024-03-26 Eastman Chemical Company Recycle content alpha olefins and fatty alcohols
US11945998B2 (en) 2019-10-31 2024-04-02 Eastman Chemical Company Processes and systems for making recycle content hydrocarbons
US11946000B2 (en) 2019-05-24 2024-04-02 Eastman Chemical Company Blend small amounts of pyoil into a liquid stream processed into a gas cracker
US12031091B2 (en) 2019-05-24 2024-07-09 Eastman Chemical Company Recycle content cracked effluent
US12104121B2 (en) 2019-11-07 2024-10-01 Eastman Chemical Company Recycle content mixed esters and solvents
US12195674B2 (en) 2021-09-21 2025-01-14 Eastman Chemical Company Using spent caustic solution from pygas treatment to neutralize halogens from liquified waste plastic
US12312540B2 (en) 2019-10-31 2025-05-27 Eastman Chemical Company Pyrolysis method and system for recycled waste
US12338211B2 (en) 2019-07-29 2025-06-24 Eastman Chemical Company Recycle content (C4)alkanal
US12398328B2 (en) 2020-02-10 2025-08-26 Eastman Chemical Company Chemical recycling of processed mixed plastic waste streams

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2459683A1 (fr) * 1979-06-22 1981-01-16 Ugine Kuhlmann Procede de stabilisation et de regeneration du catalyseur d'hydroformylation du propene

Citations (5)

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US2327066A (en) * 1938-09-19 1943-08-17 Roelen Otto Production of oxygenated carbon compounds
US2548159A (en) * 1947-01-17 1951-04-10 Shell Dev Group viii silicate catalyst on nonsiliceous support
US2691046A (en) * 1948-04-22 1954-10-05 Eastman Kodak Co Process for the manufacture of oxygenated compounds with improved catalysts
US2694730A (en) * 1951-10-02 1954-11-16 Universal Oil Prod Co Derivatives of bicyclooctene hydrocarbons and production thereof
US2744936A (en) * 1952-02-09 1956-05-08 Exxon Research Engineering Co Oxo synthesis using cobalt salt of cobalt carbonyl

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2327066A (en) * 1938-09-19 1943-08-17 Roelen Otto Production of oxygenated carbon compounds
US2548159A (en) * 1947-01-17 1951-04-10 Shell Dev Group viii silicate catalyst on nonsiliceous support
US2691046A (en) * 1948-04-22 1954-10-05 Eastman Kodak Co Process for the manufacture of oxygenated compounds with improved catalysts
US2694730A (en) * 1951-10-02 1954-11-16 Universal Oil Prod Co Derivatives of bicyclooctene hydrocarbons and production thereof
US2744936A (en) * 1952-02-09 1956-05-08 Exxon Research Engineering Co Oxo synthesis using cobalt salt of cobalt carbonyl

Cited By (61)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3081357A (en) * 1960-05-24 1963-03-12 Du Pont Process for producing alkanediols
US3239566A (en) * 1960-07-22 1966-03-08 Shell Oil Co Hydroformylation of olefins
US3352924A (en) * 1963-01-23 1967-11-14 Exxon Research Engineering Co Carbonylation reactions
US3501531A (en) * 1964-12-15 1970-03-17 Ethyl Corp Hydroformylation process
US3509221A (en) * 1965-07-09 1970-04-28 Shell Oil Co Production of cyclooctanemethanol
US3446839A (en) * 1965-09-20 1969-05-27 Shell Oil Co Production of alkyl hydroxy-pivalates
US3318913A (en) * 1965-09-22 1967-05-09 Shell Oil Co Process for producing alpha-methylgamma-butyrolactone
US3487112A (en) * 1967-04-27 1969-12-30 Monsanto Co Vapor phase hydroformylation process
DE1793069A1 (de) * 1967-08-03 1972-02-03 Union Carbide Corp Verfahren zur Herstellung sauerstoffhaltiger Produkte
US3887489A (en) * 1972-11-24 1975-06-03 Monsanto Co Rhodium catalyst regeneration method
US4113781A (en) * 1973-08-11 1978-09-12 Basf Aktiengesellschaft Phenylpropanals
US4101450A (en) * 1977-05-09 1978-07-18 Celanese Corporation Catalyst for production of acetic acid
JPS5416418A (en) * 1977-06-21 1979-02-07 Johnson Matthey Co Ltd Process for preparing linear aldehyde
US4147725A (en) * 1978-03-22 1979-04-03 The Dow Chemical Company Process for preparing aniline compounds from amides with rhodium
US4229324A (en) * 1978-05-04 1980-10-21 Kao Soap Company, Limited Tricyclo-α,β-unsaturated aldehyde
US4270007A (en) * 1978-11-16 1981-05-26 Henkel Kommanditgesellschaft Auf Aktien Perfume aldehydes from hydroformylation of caryophyllene
US4283561A (en) * 1978-11-16 1981-08-11 Henkel Kommanditgesellschaft Auf Aktien Mixture of aldehydes resulting from hydroformylation of α-terpinene
US4334100A (en) * 1978-11-16 1982-06-08 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Production of aldehydes
US4262147A (en) * 1979-03-16 1981-04-14 The Dow Chemical Company Hydroformylation of dicyclopentadiene to its dimethanolic derivatives
US4320032A (en) * 1979-11-16 1982-03-16 Suntech, Inc. Catalyst for hydrogenation of aromatic dinitriles
US4298499A (en) * 1980-07-14 1981-11-03 Uop Inc. Recovery of catalysts
US4312779A (en) * 1980-09-25 1982-01-26 Uop Inc. Recovery of catalysts
US4340569A (en) * 1981-03-06 1982-07-20 The Halcon Sd Group, Inc. Treatment of carbonylation residues
US4340570A (en) * 1981-03-06 1982-07-20 The Halcon Sd Group, Inc. Recovery of rhodium from carbonylation residues
US4341741A (en) * 1981-03-06 1982-07-27 The Halcon Sd Group, Inc. Recovery of rhodium from carbonylation residues
US4400547A (en) * 1981-04-10 1983-08-23 Eastman Kodak Company Hydroformylation process utilizing an unmodified rhodium catalyst and the stabilization and regeneration thereof
WO1982003856A1 (en) * 1981-05-01 1982-11-11 Kodak Co Eastman Hydroformylation process
US4388476A (en) * 1981-05-01 1983-06-14 Eastman Kodak Company Hydroformylation process with rhodium catalyst and oxygen stabilization thereof
US4476237A (en) * 1981-05-28 1984-10-09 The Halcon Sd Group, Inc. Separation of tars from carbonylation reaction mixtures
US4476238A (en) * 1981-05-28 1984-10-09 The Halcon Sd Group, Inc. Separation of tars from carbonylation reaction mixtures
US4388477A (en) * 1981-06-02 1983-06-14 Eastman Kodak Company Hydroformylation process employing unmodified rhodium-cobalt catalyst
EP0082641A1 (en) * 1981-12-18 1983-06-29 The Standard Oil Company Catalysts for the production of alcohols from olefins and synthesis gas and process employing such catalysts
US4361711A (en) * 1981-12-18 1982-11-30 The Standard Oil Company Alcohols from olefins and synthesis gas
US4460795A (en) * 1982-03-02 1984-07-17 International Flavors & Fragrances Inc. Process for preparing mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives
US4448984A (en) * 1982-03-02 1984-05-15 International Flavors & Fragrances Inc. Mono-oxomethyl substituted polyhydrodimethanonaphthalene derivatives
US4587364A (en) * 1984-05-21 1986-05-06 Eastman Kodak Company Hydroformylation process employing unmodified osmium-cobalt catalyst
US4694109A (en) * 1986-06-13 1987-09-15 Eastman Kodak Company Chelate ligands for low pressure hydroformylation catalyst and process employing same
US4742178A (en) * 1986-11-10 1988-05-03 Eastman Kodak Company Low pressure hydroformylation of dienes
US5468419A (en) * 1987-02-09 1995-11-21 Mitsubishi Chemical Corporation Preparation of C9 alcohol mixture and plasticizer
US5189105A (en) * 1987-02-09 1993-02-23 Mitsubishi Chemical Industries Limited Alcohol mixture for plasticizer
US5081313A (en) * 1989-06-22 1992-01-14 Basf Aktiengesellschaft Process for the preparation of 2,3-dialkoxypropanals
US5919987A (en) * 1994-03-16 1999-07-06 Basf Aktiengesellschaft Preparation of alcohols and/or aldehydes
US5410091A (en) * 1994-06-02 1995-04-25 Quimica Oxal C.A. Rhodium catalyzed oxo process in tubular reactor
US6365782B1 (en) 1999-07-02 2002-04-02 Mitsbushi Gas Chemical Company, Inc. Production of tricyclodecane dicarbaldehyde, pentacyclopentadecane dicarbaldehyde and corresponding dimethanols
EP1138751A3 (en) * 2000-03-27 2002-12-18 Toyota Jidosha Kabushiki Kaisha Method of manufacturing oxygenated fuel
US6660889B2 (en) 2000-03-27 2003-12-09 Toyota Jidosha Kabushiki Kaisha Method of manufacturing oxygenated fuel
US11946000B2 (en) 2019-05-24 2024-04-02 Eastman Chemical Company Blend small amounts of pyoil into a liquid stream processed into a gas cracker
US11365357B2 (en) 2019-05-24 2022-06-21 Eastman Chemical Company Cracking C8+ fraction of pyoil
US12098338B2 (en) 2019-05-24 2024-09-24 Eastman Chemical Company Cracking c8+ fraction of pyoil
US12031091B2 (en) 2019-05-24 2024-07-09 Eastman Chemical Company Recycle content cracked effluent
WO2021021902A1 (en) 2019-07-29 2021-02-04 Eastman Chemical Company Process for the preparation of polyesters with recycled monomers from pyrolysis and methanolysis
US12338211B2 (en) 2019-07-29 2025-06-24 Eastman Chemical Company Recycle content (C4)alkanal
WO2021021855A1 (en) 2019-07-29 2021-02-04 Eastman Chemical Company Recycle content cyclobutane diol polyester
US11787754B2 (en) 2019-10-31 2023-10-17 Eastman Chemical Company Processes and systems for making recycle content hydrocarbons
US11945998B2 (en) 2019-10-31 2024-04-02 Eastman Chemical Company Processes and systems for making recycle content hydrocarbons
US12312540B2 (en) 2019-10-31 2025-05-27 Eastman Chemical Company Pyrolysis method and system for recycled waste
US11319262B2 (en) 2019-10-31 2022-05-03 Eastman Chemical Company Processes and systems for making recycle content hydrocarbons
US11939534B2 (en) 2019-11-07 2024-03-26 Eastman Chemical Company Recycle content alpha olefins and fatty alcohols
US12104121B2 (en) 2019-11-07 2024-10-01 Eastman Chemical Company Recycle content mixed esters and solvents
US12398328B2 (en) 2020-02-10 2025-08-26 Eastman Chemical Company Chemical recycling of processed mixed plastic waste streams
US12195674B2 (en) 2021-09-21 2025-01-14 Eastman Chemical Company Using spent caustic solution from pygas treatment to neutralize halogens from liquified waste plastic

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